DE3780349T2 - Deaktivierung eines phosphoniumsalzkatalysators. - Google Patents

Deaktivierung eines phosphoniumsalzkatalysators.

Info

Publication number: DE3780349T2
Authority: DE; Germany
Prior art keywords: catalyst; salt catalyst; group; hydrocarbylphosphonium; sulfonic acid
Prior art date: 1986-04-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

DE8787200731T

Other languages

German (de)

English (en)

Other versions

DE3780349D1 (de

Inventor

Harry Frank

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-04-30

Filing date

1987-04-15

Publication date

1992-12-17

1987-04-15 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1992-08-20 Publication of DE3780349D1 publication Critical patent/DE3780349D1/de

1992-12-17 Application granted granted Critical

1992-12-17 Publication of DE3780349T2 publication Critical patent/DE3780349T2/de

2007-04-16 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 55
150000004714 phosphonium salts Chemical class 0.000 title abstract description 11
230000004927 fusion Effects 0.000 claims abstract description 32
229920000647 polyepoxide Polymers 0.000 claims abstract description 20
-1 hydrocarbyl phosphonium salt Chemical class 0.000 claims abstract description 16
239000003822 epoxy resin Substances 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 9
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000004593 Epoxy Substances 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
150000002989 phenols Chemical class 0.000 claims description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 25
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 15
230000009849 deactivation Effects 0.000 abstract description 11
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 23
239000003795 chemical substances by application Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
229940106691 bisphenol a Drugs 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000376 reactant Substances 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
229910006069 SO3H Inorganic materials 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
SRWLXBHGOYPTCM-UHFFFAOYSA-M acetic acid;ethyl(triphenyl)phosphanium;acetate Chemical compound CC(O)=O.CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SRWLXBHGOYPTCM-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052792 caesium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000007499 fusion processing Methods 0.000 description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 2
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
WCUDAIJOADOKAW-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1 WCUDAIJOADOKAW-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
HVFBISAATINJPF-UHFFFAOYSA-L triphenyl(triphenylphosphaniumylmethyl)phosphanium;dibromide Chemical group [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HVFBISAATINJPF-UHFFFAOYSA-L 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Catalysts (AREA)
Compositions Of Macromolecular Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DE8787200731T 1986-04-30 1987-04-15 Deaktivierung eines phosphoniumsalzkatalysators. Expired - Lifetime DE3780349T2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/858,311 US4692504A (en)	1986-04-30	1986-04-30	Deactivation of phosphonium salt catalyst

Publications (2)

Publication Number	Publication Date
DE3780349D1 DE3780349D1 (de)	1992-08-20
DE3780349T2 true DE3780349T2 (de)	1992-12-17

Family

ID=25328000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE8787200731T Expired - Lifetime DE3780349T2 (de)	1986-04-30	1987-04-15	Deaktivierung eines phosphoniumsalzkatalysators.

Country Status (13)

Country	Link
US (1)	US4692504A (pt)
EP (1)	EP0244015B1 (pt)
JP (1)	JPS62262749A (pt)
KR (1)	KR870010101A (pt)
CN (1)	CN1009650B (pt)
AT (1)	ATE78274T1 (pt)
AU (1)	AU584796B2 (pt)
BR (1)	BR8702060A (pt)
CA (1)	CA1309548C (pt)
DE (1)	DE3780349T2 (pt)
ES (1)	ES2041674T3 (pt)
GR (1)	GR3005295T3 (pt)
ZA (1)	ZA873012B (pt)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4946817A (en) *	1984-07-17	1990-08-07	The Dow Chemical Company	Latent catalysts for epoxy-containing compounds
US5503937A (en) *	1984-07-17	1996-04-02	The Dow Chemical Company	Curable composition which comprises adducts of heterocyclic compounds
US5202051A (en) *	1987-04-29	1993-04-13	Shell Oil Company	Stabilization of epoxy/nitroparaffin solutions
US4933420A (en) *	1988-09-23	1990-06-12	The Dow Chemical Company	Epoxy resins containing phosphonium catalysts
US4939112A (en) *	1988-10-06	1990-07-03	James River Paper Company, Inc.	Catalyst for synthesis of vesicular phenoxy resins
US5310854A (en) *	1989-08-23	1994-05-10	The Dow Chemical Company	Epoxy resin composition and process therefor
US4981926A (en) *	1990-02-06	1991-01-01	The Dow Chemical Company	Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent
US5208317A (en) *	1990-02-06	1993-05-04	The Dow Chemical Company	Composition comprising epoxy resin and cationic amine phosphonium catalyst
US5140079A (en) *	1990-02-06	1992-08-18	The Dow Chemical Company	Latent, curable, catalyzed mixtures of epoxy-containing and phenolic-hydroxyl-containing compounds containing compounds or complexes formed from contacting organic phosphines or arsines with weak nucleophilic acids
US5169473A (en) *	1990-05-21	1992-12-08	The Dow Chemical Company	Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions
US5721323A (en) *	1990-05-21	1998-02-24	The Dow Chemical Company	Cure inhibited epoxy resin compositions and laminates prepared from the compositions
ZA913801B (en) *	1990-05-21	1993-01-27	Dow Chemical Co	Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom
US5202407A (en) *	1992-01-24	1993-04-13	The Dow Chemical Company	Precatalyzed catalyst compositions, process for preparing epoxy resins curable compositions, articles resulting from curing the resultant compositions
DE19547786A1 (de) *	1995-12-20	1997-06-26	Basf Lacke & Farben	Aufbau von modifizierten Epoxidharzen für die kathodische Elektrotauchlackierung mit Katalysator-Desaktivierung und Diolmodifizierung
JP2004210672A (ja) *	2002-12-27	2004-07-29	Nippon Chem Ind Co Ltd	ビスホスホニウム塩化合物及びその製造方法
CN1319446C (zh) *	2004-09-27	2007-06-06	深圳市绿微康生物工程有限公司	新型生物农药－松刚霉素生产方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3477990A (en) *	1967-12-07	1969-11-11	Shell Oil Co	Process for reacting a phenol with an epoxy compound and resulting products
US3547885A (en) *	1968-03-08	1970-12-15	Sun Oil Co	Process for curing polyepoxides with anhydrides and phosphonium halide catalysts therefor
DE2416227C3 (de) *	1974-04-03	1980-04-30	Chemische Werke Huels Ag, 4370 Marl	Verfahren zur Entfernung von Katalysatoren aus flüssigen Reaktionsgemischen
US3978027A (en) *	1975-05-07	1976-08-31	Shell Oil Company	Process for reacting a phenol with an epoxy compound
US4352918A (en) *	1980-12-04	1982-10-05	The Dow Chemical Company	Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
US4370465A (en) *	1980-12-04	1983-01-25	The Dow Chemical Co.	Epoxy resins having improved physical properties when cured
US4410596A (en) *	1980-12-04	1983-10-18	The Dow Chemical Co.	Process for preparing epoxy resins having improved physical properties when cured
US4366295A (en) *	1981-06-01	1982-12-28	The Dow Chemical Company	Stable precatalyzed epoxy resin compositions
US4496709A (en) *	1982-06-23	1985-01-29	The Dow Chemical Company	Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst
US4438254A (en) *	1983-02-28	1984-03-20	The Dow Chemical Company	Process for producing epoxy resins
GB8420817D0 (en) *	1984-08-16	1984-09-19	Dow Chemical Rheinwerk Gmbh	Preparing epoxy resins

1986
- 1986-04-30 US US06/858,311 patent/US4692504A/en not_active Expired - Fee Related
1987
- 1987-04-07 CA CA000533994A patent/CA1309548C/en not_active Expired - Fee Related
- 1987-04-15 ES ES198787200731T patent/ES2041674T3/es not_active Expired - Lifetime
- 1987-04-15 EP EP87200731A patent/EP0244015B1/en not_active Expired - Lifetime
- 1987-04-15 AT AT87200731T patent/ATE78274T1/de active
- 1987-04-15 DE DE8787200731T patent/DE3780349T2/de not_active Expired - Lifetime
- 1987-04-28 KR KR870004122A patent/KR870010101A/ko not_active Application Discontinuation
- 1987-04-28 CN CN87103127A patent/CN1009650B/zh not_active Expired
- 1987-04-28 JP JP62103485A patent/JPS62262749A/ja active Pending
- 1987-04-28 BR BR8702060A patent/BR8702060A/pt not_active IP Right Cessation
- 1987-04-28 AU AU72149/87A patent/AU584796B2/en not_active Ceased
- 1987-04-28 ZA ZA873012A patent/ZA873012B/xx unknown
1992
- 1992-07-29 GR GR920401626T patent/GR3005295T3/el unknown

Also Published As

Publication number	Publication date
ES2041674T3 (es)	1993-12-01
ATE78274T1 (de)	1992-08-15
KR870010101A (ko)	1987-11-30
AU584796B2 (en)	1989-06-01
CN87103127A (zh)	1987-12-30
AU7214987A (en)	1987-11-05
JPS62262749A (ja)	1987-11-14
ZA873012B (en)	1987-11-25
DE3780349D1 (de)	1992-08-20
EP0244015B1 (en)	1992-07-15
CA1309548C (en)	1992-10-27
EP0244015A2 (en)	1987-11-04
EP0244015A3 (en)	1989-02-01
CN1009650B (zh)	1990-09-19
BR8702060A (pt)	1988-02-09
US4692504A (en)	1987-09-08
GR3005295T3 (pt)	1993-05-24

Legal Events

Date	Code	Title	Description
1993-08-12	8364	No opposition during term of opposition
1995-04-13	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE3780349T2 (de)	1992-12-17	Deaktivierung eines phosphoniumsalzkatalysators.
DE69519807T2 (de)	2001-07-19	Verfahren zur herstellung von epoxyverbindungen
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DE1103580B (de)	1961-03-30	Verfahren zur Herstellung von im wesentlichen monomere Glycidylpolyaether enthaltenden Glycidyl-polyaethern mehrwertiger Phenole
DE1812972A1 (de)	1969-07-10	Verfahren zur Herstellung von Phenylhydroxyaethern
DE2263175C2 (de)	1982-08-26	Verfahren zur Herstellung von Polyepoxiden
GB2135674A (en)	1984-09-05	A process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the process
DE2947469A1 (de)	1981-06-04	Verfahren zur herstellung von glycidylaethern ein- oder mehrwertiger phenole
CH658457A5 (de)	1986-11-14	Difunktionelles epoxid.
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DE3787519T2 (de)	1994-01-20	Eine Zusammensetzung enthaltend ein Polyepoxyd und ein Katalysator für Epoxydvorverlängerungsverfahren, und ein Verfahren zur Herstellung von vorverlängerten Epoxydharzen.
KR900006913B1 (ko)	1990-09-24	에폭시 수지의 작용성을 증가시키는 방법
US4624975A (en)	1986-11-25	Process for stabilizing the hydrolyzable chloride content in epoxy resins
US4269952A (en)	1981-05-26	Preparation of glycidyl polyarylethers
US4585838A (en)	1986-04-29	Process for preparing epoxy resins containing low levels of total halide
DE4121791C2 (de)	2001-02-22	Verfahren zur Herstellung von substituierten Cycloalkylidenbisphenolen
EP0232910B1 (en)	1990-04-25	Methods for preparing advanced epoxy or phenoxy resins with low aliphatic halide content
US4313886A (en)	1982-02-02	Process for preparing liquid epoxy resins
DE1961888B2 (de)	1978-08-03	Verfahren zur Herstellung von Glycidyläthern ein- und mehrwertiger Phenole
DE2028136B2 (de)	1980-11-13	Verfahren zur Herstellung von niedermolekularen Polyglycidylethern
US4273915A (en)	1981-06-16	Process for the preparation of glycidyl polyethers of polyphenols
DE69400126T2 (de)	1996-10-02	Verfahren zur Herstellung von Alphaglycolgruppen enthaltenden Glycidyletherharzen
KR830001351B1 (ko)	1983-07-14	폴리페놀의 글리시딜 폴리에테르류의 제조 방법
US3062840A (en)	1962-11-06	Epoxy-substituted polyhydric phenols
DE2643336C3 (de)	1978-10-26	Herstellung von festen Glycidyläthern mehrwertiger Phenole